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Then in second place: Cromartie High School. Dubbed. No I'm serious. NO I'm serious!
They are only eleven minute episodes and it's got cheesy voice acting and bad animation but that's all part of the comedy! Take a look, I'm pretty sure it's on YouTube.

Third is where I'd rank Working! (both seasons)
Clannad and K-ON! both have amazing funny moments but Working! is less Slice of Life and more pure comedy. You get way more laughs and the character based humor in impeccable.

Then of course there's Lucky Star and Azumanga Daioh

If you're looking for something with more of a story Slayers is like a hybrid of comedy and fantasy.

People may get pissed at me for this but Ouran High School Host Club is both funny and entertaining.

From what I gather there's really no plot. Each country is a different character and they just interact with each other. They do some historic events I think but not much. Unless there's a plot later on. I've only watched Axis Powers and a bit of World Series.

Panty & Stocking with Garterbelt, if you like hearing swear words in hilarious Engrish and dirty jokes thrown every 3 seconds, coupled with a Western Cartoon style that parodies other Western movies/tv shows.

It's one of those shows you either love or hate.

I also highly recommend Sket Dance, although I personally prefer the manga over the anime.

Both really crazy comdies by studio shaft. Pani Poni Dash also falls under the category, but I didn't enjoy it quite as much as the above.

School Rumble (once you get past the first few episodes)
Kodocha (sort of a dramedy really)
Ranma 1/2 (depends on the episode, some are hilarious, some are stinkers. season 1 is really strong regardless)

Panty & Stocking with Garterbelt, if you like hearing swear words in hilarious Engrish and dirty jokes thrown every 3 seconds, coupled with a Western Cartoon style that parodies other Western movies/tv shows.

It's one of those shows you either love or hate.

I was going to mention this, but like you said it's a love-hate thing. I still suggest that people should give it a try though if they're cool with filthy jokes or cool with people trying to make filthy jokes.

That's not really anime. Well, I mean it's based around the anime and it uses the clips from the series but it's more of just a silly fandub. That said it's a really frickin' funny one (and this is coming from someone who just only knows the basics of DBZ and didn't watch the TV series.)

Hard to say... really. I think the funniest one I've see so far is Azumanga Daioh, though I think I laughed more with CLANNAD because of how well it handled its comedic moments. Though I'm sure that if I sat down to watch Bobobo-bo Bo-bobo, it'd be the funniest one I'd see. Just a guess, though.

Of course, if you really want the cheap laughs and giggles, go watch some dubs from the 90s. Or heck, the dub for the first two seasons of Digimon is so freakin' cheesy, it's funny. There is always something to laugh at.